Formal total synthesis of FK506. Concise construction of the C(10)-C(34) segment via an effective coupling tactic

Amos B. Smith, Kwunmin Chen, Darius J. Robinson, Leif M. Laakso, Karl J. Hale

Research output: Contribution to journalArticle

33 Citations (Scopus)

Abstract

A formal total synthesis of the potent immunosuppressant FK506 (1) has been achieved via a concise construction of the Merck advanced intermediate (-)-2. Key features of the successful strategy include stereocontrolled σ-bond installation of the trisubstituted olefin moieties and an efficient coupling of the C(24)-C(34) dithiane (-)-10 with the C(10)-C(23) α-silyloxy primary iodide (-)-9.

Original languageEnglish
Pages (from-to)4271-4274
Number of pages4
JournalTetrahedron Letters
Volume35
Issue number25
DOIs
Publication statusPublished - 1994 Jun 20

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Alkenes
Iodides
Tacrolimus
Immunosuppressive Agents
dithiane

ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

Cite this

Formal total synthesis of FK506. Concise construction of the C(10)-C(34) segment via an effective coupling tactic. / Smith, Amos B.; Chen, Kwunmin; Robinson, Darius J.; Laakso, Leif M.; Hale, Karl J.

In: Tetrahedron Letters, Vol. 35, No. 25, 20.06.1994, p. 4271-4274.

Research output: Contribution to journalArticle

Smith, Amos B. ; Chen, Kwunmin ; Robinson, Darius J. ; Laakso, Leif M. ; Hale, Karl J. / Formal total synthesis of FK506. Concise construction of the C(10)-C(34) segment via an effective coupling tactic. In: Tetrahedron Letters. 1994 ; Vol. 35, No. 25. pp. 4271-4274.
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